29 Incredibly Inspiring Stories From Wingmen Who Took The Extra Step To Help Out Their Friend

These people are saints. If you want to read more, check out the Reddit thread here.

1. [deleted]

In our dorm all of the window screens were fastened by screws. There were no female visitors allowed after 10:00PM. I removed the screws from my ground floor window, and passed the word to the entire dorm that any visitors were welcome to pass through. It wasn’t long before I had girls knocking on my window at all hours of the night. I would remove the screen, open the window, help them climb through, send them in the right direction, and replace the screen and close the window. The Resident Assistants never knew, as my room was directly opposite from the front office. So…you could say I was a wingman for the entire dorm.

2. DontTrustNeverSober

I had a party at my house and a lot of people ended up crashing there because they were way too drunk to drive home. All the rooms were occupied except for mine. My buddy met this girl and really wanted to hook up with her but had no where to do it, so I offered up my lovely, innocent bed to spread his baby gravy all over. I slept on the ground in the other room and woke up the next morning with a note thanking me, a $20 bill, and my sheets in the washing machine.

3. Xuanwu

Buddy of mine was talking to a girl who was making not so subtle hints that he should get over there. He unfortunately was about 90 minutes by car away and didn’t even have a car. As it was 1am he didn’t even have public transport to avail himself of.

He mentioned his dilemma to a small social group and I decided he was losing his V-card that night. I drove 20 minutes to his house, then 90 up the coast to drop him off near 3am.

Mission was a complete success.

4. ThemFeels

Went out with a large group of friends for my best friends birthday, ended up in a club. My friend had been drinking heavily throughout the day, and we were meant to be meeting up with a group of girls later on, one of whom was a long time interest he’d had. Just as we arrived at the club, he threw up, EVERYWHERE. I mean just all down himself and just looked horrible. Anyway, as was expected, he sobered up pretty soon after, and just kept saying how he couldn’t believe he’d blown his chance with this girl. A few friends said he should just go home and call it a night but he was getting more and more upset because apparently she’d said it was a sure thing if he met up with her. Now, he didn’t have much luck with the girls and I really wanted this for him, so I took him to a nearby alley and (after actually having to convince him to make this happen) got him to switch clothes with me. He went in, had a great time, and has now been with the girl for about 3 years. I went home in a taxi covered in sick.

TL;DR I changed into my friends sick covered clothes so he could continue his night out and get the girl.

5. nottodaythecops

only get partial credit for this one because I didn’t actually do anything, but it’s still my favorite. So, every year a bunch of friends and I go to DragonCon in Atlanta. Last year I couldn’t go because I was deployed in Afghanistan, so my buddy decided to get a 5 foot tall print of a picture of me, paste it to a board, and carry it around the whole time. Apparently it was a great conversation starter and the whole “I’m bringing my friend here in spirit” thing played extremely well. He ended up sleeping with some girl dressed as Lara Croft.

6. namzi

So I had this friend, a white and nerdy type, 18 and eager to lose his virginity. One night I decided to take him out to a house party and introduce him to another single friend, a hot chick (a naughty librarian type a girl). A couple of drinking late for both of them, they really start to hit it off, so I walk off to do my thing. The night is great, dancing, drinking and fucking around. Then I see my friend at the bar/kitchen bench surrounded by 2 guy pushing, and yelling at him. Naturally I walk over to sort this out.

Apparently he spilled a drink of one of the guys, and the guy was pissed that his socks are wet. I try to talk things out without resorting to violence, which clearly isn’t working. So I tell my friend to go back to the girl, and I stay back and deal with this asshole. Thus I ended up getting into a fight with these two blokes outside (mainly getting the shit beat out of me) while my friend was getting his brains fucked out in the bedroom upstairs. Still to this day haven’t told about the fight.

7. yipjumpmusic

So this girl was really into my roommate and she didn’t know how to go about getting him interested in her. I didn’t mention that he was already into her because I figured things would work, nature would take over. but I know that my roommate never really had a girlfriend that liked to actively give blowjobs and that he really wanted a girlfriend who he wouldn’t feel bad about asking for one. So I texted her a little “guide to my roommate” and inside i explained that his biggest turn on and favorite thing ever is spontaneous blow jobs.

After a few days, they started seeing each other. Months later I had asked how they were doing and he explained, “Man, I don’t know what her deal is but she is crazy about blow jobs! I’ve never had so many in my life, it’s fantastic!”

I felt like a child’s parent after hiding money from the tooth fairy under their pillow.

8. hagen0

I had a friend who was “open” visiting and she didn’t want to sleep on the couch so I told her that she should just sleep in my roommates bed with him. She was good looking and he was/is a neckbeard, so he was happy to have a hot girl in his bed.

After a couple of nights, she tells me that he hasn’t made a move and it’s getting annoying. Of course, she is unwilling to make a move either so they just stay up all night talking about painfully stupid shit that I’m sure no man cares about, but he is entertaining it because of the chance he might get some.

The next day I ask her if he’s made a move – she responds “He’s still being such a sweet guy, but I saw some condoms, I’m not sure if he is trying to give me a hint.”

I then ask him if he’s hooked up with her yet and he tells me “No, but I found condoms on my nightstand that I didn’t put there.”

My response, “She might be giving you a hint, go for it!”

He goes for it and bangs her for the next week.

They still don’t know it was I who bought the condoms and strategically placed them on his stand without telling either of them.

9. Blonde_Bomber

My dorm neighbor was having his girlfriend over but had nowhere to fool around since his roommate also had a girl over. Being nice, I gave him my room and planned to sleep in my other neighbors room.

I slept in my neighbor-on-the-other-side’s room… Until he starts having phone sex with HIS girlfriend.

I ended up sleeping in the hallway on the floor with a pillow and a quilt.

10. whatiwawa

Not really crazy but I was always in on some of the magic tricks that a buddy would do at a bar. This involved stuffing a card into a girl’s purse with her back turned to me/pretending I was just a stranger who miraculously has her card in my coat pocket.

This system actually worked to some degree…

11. friendlyfunfunman

This girl was really into bi guys, so I kissed my friend in front of her.

  • I am a guy
  • My friend is a guy
  • My friend did get laid
  • The kiss was aight 6/10
  • We still homies

12. MasteroftheD

At a bar and saw my friend checking out a pretty busty girl. I went over to her, bought her a drink, told her it was from him. She looked over at him and smiled. I made small talk for a while and could tell she was into him and she was the kind of girl that would have a one night stand. I could tell I wasn’t doing much though so it was time to bring out the big guns. I topped off my drink, and just told her bluntly, “This guy’s into you. He’s got a big dick.” And walked away. He got laid that night.

13. OJs_Lawyer

My friend was sleeping over at my house. My parents and brother were all sleeping upstairs while we were downstairs watching tv, playing video games and shit. At around 1 am he asks if this girl can come over (he REALLY wants to get with this girl, and I don’t want to turn him down so I reluctantly agree, on the condition that she’s quiet.) The three of us are hanging out and I make some excuse to leave the room so my friend can have some alone time with this girl. I’m upstairs in my room when I start hearing loud moans. This is bad news for me, but great news for my friend, he’s losing his virginity to a girl he really likes. I hear stirring in the next room and I know that their bout of loud lovemaking has woken my parents. The last thing I want is for my confused father to walk in on my friend fucking this girl in my basement. What do I do? I go to pornhub, click on the first video I see, crank that shit to 100 on my speakers and let it play for the ~three minutes that my buddy ended up lasting. My dad ended up coming into my room, discovering the source of the noise (I even threw in some fapping motion under the covers) and awkwardly leaving. My buddy ended up having “the best fucking time ever bro,” but jesus there were some awkward glances exchanged between my parents and I the next morning.

14. krabbby

Well it wasn’t me. I was the friend.

This was in high school. My friend and me were at a party before graduation. There was this girl who I was really interested in. He brought her over, built me up, and we ended up hooking up. We were all various levels of drunk at that point, but he ended up volunteering to drive us home in my car to help us out. He dropped us off and asked if he could take the car for the night and bring it back the morning after. I agreed so he wouldn’t be stuck there. I went inside and it went okay.

The next morning, the car wasn’t there. I was upset because I figured I would at least be able to give her a ride home. I tried calling him but got no answer. We ended up walking somewhere to get breakfast. We got there, sat down, and my phone rang. It was a friend of mine and my friend. He was asking me if I heard what happened, I said no. He sounded upset and I immediately got a bad feeling.

My friend had gotten into an accident, totaling the car. He died in the hospital of internal bleeding. We sat at the table for what seemed like forever, both feeling guilty as hell in some way. Ill never forget my friend, who died after setting me up with my first time, and girlfriend of 2 years.

15. W3dn3sday

I count Kevin Spacey as my best wingman. Not really crazy but still awesome. Probably will not be seen. But Kevin Spacey is awesome in person. When I first met him I thought he would be a total dick. I was visiting New York with a friend of mine and my friend took me to my first Broadway play. Which being from a small town in the south was fucking spectacular. I mean the effects and everything. I recommend to go see a play in New York to everyone. But anyway we were walking out of the theater and my friend who hid his pint in his leather jacket going in. Asked if I wanted some so I said sure. Then it his me like a mack truck like how about we go in the bathroom and drink because no cops should be around. So we go into the bathroom and there is this one guy pissing so we act like we are washing our hands which seemed like forever (we got pretty toasted before the show). The guy walks out and we start swigging away on it to finish it.

So in comes Kevin Spacey, my friend and I are dumbfounded…..my first thought was hide the bottle in my hand and my second thought was this is Kevin Spacey he smoked weed in American Beauty. So he just walks in and gives us a nod, uses the urinal and while he’s pissing says (to this day I will never forget it), “Are you here for the show or to watch me piss?”…Since I was lit I blurted out we are here to drink. My friend slaps me upside the head and nothing but silence. He zips up and turns around and says good so am I. He whips out a flask and we pass him our pint. We bullshit for a couple minutes, he says it was nice to meet you and whatever….but the best thing was is this….I told him this is my first time in New York and was wondering if there was any good bars. He said try such and such….my friend and I looked at each other then he left. We walked out thinking he probably thought we were gay….so long story short…we go to this bar and mention Kevin Spacey said come here after we got out of this show.

Apparently he called ahead and told the guy what we were wearing and everything was comped. We did not run up a huge tab or anything but we were sat in the VIP section and everyone looked at us like we were gods. Also we got laid that night. The tab was probably like three hundred dollars and we told the manager we wanted to pay….he said no….so we left the woman who waited on us a $200 tip….also we took a couple women to our hotel room and had some more fun. My friend passed out after doing Tequila shots with the women…..so long story short Kevin Spacey hooked me up with my first and only threesome to this day I do not tell this very often because no one believes me. But rest assure if you meet him he is a godsend.

16. ConquistDelTaco

A large group of us decided it would be fun to break into an outdoor pool late at night and go for a swim. A girl that one of my buddies had been interested in for some time was going to be there, so naturally he made an appearance too. They ended up chatting for quite sometime, and it looked like they were going to go home together. The night started to die down, and the only people left were myself, my buddy, the girl, and another friend of mine. As we’re preparing to leave the pool, the police show up (just 1 car, so a couple of officers), and are about to arrest us. I can see the massive look of disappointment on my buddy’s face, so I take a deep breath and shout “WILDCARD BITCHES!” toss a huge bin of pool toys into the pool, and jump on top of the police cruiser naked. Fortunately, both of the officers chased after me, and my buddy and the girl managed to run away. They hooked up that night, and have been dating for 8 months now.

TL;DR Wildcard Bitches

17. Nerflord

Joined a racist/nationalist/homophobic youth organisation (it had certain controversial views on border protection and homosexual marriage that I was ignorant of) so she could score some ignorant douchenozzle.

I’m Chinese Australian. I basically joined a group to tell my own people they should go home.

18. AllUrMemes

I have a moderate gambling problem.

Went to Atlantic City with some friends and actually had a successful night, making about $500 at the poker table. It was about 2AM and I for once made the responsible decisions to go to bed at a reasonable hour, and while I was ahead.

I am the first one back to the room and go to sleep. Some time later, my friend comes back with a young lady. They make small talk about her life collecting tolls and living under bridges, harassing billy goats, etc.

It soon becomes clear that my friend intends to bed this girl. He makes a move but she rebuffs him, uncomfortable with the fact that I am (they think) sleeping in the other bed. I was going to just continue to lay there so as to cock-block my friend and prevent him from making this mistake, but it became clear my friend really wanted to do this. So I “awoke”, and said “gosh that was a great nap, I feel refreshed and ready to go back down to the casino.”

Since there was nothing else to do, I started gambling again. I didn’t want to go back to the poker table so I sat down at the slots, where I proceeded to piss away the $500 profit and another $300 for good measure.

TL;DR: Have a gambling problem, went back to a casino so my friend could fuck a fat chick, lost $800.

Alternative TL;DR: Essentially paid for the world’s most ugliest $800 prostitute for my friend.

19. Lopsidedbuilder69

I shit my pants for a friend. A group of us were going out to drink and a friend of mine (let’s call him Jack) wanted to bring a girl that he liked along, so we all said yes. Well about 3 hours into the night, said friend has too much to drink and throws up, which puts the girl off a bit. She begins getting chummy with me since I’m the only other single guy in the group (the others brought girls or had girlfriends). She starts rubbing up, getting touchy etc, and I ask her why she isn’t talking to Jack anymore, and she says it’s cause she thinks vomiting is gross. I, in my stupid drunken state, assume (correctly) if I do something grosser she’ll go back to Jack, so I claim I shit myself. She laughs and says she’d be able to smell it, so I went ahead and did it right there. Plan worked, he got laid later that night, I washed in the woods with a water bottle and notebook paper and then went commando in my friend’s short running shorts he had his car.

20. mayest

I am a girl and pretended to be “with” my guy friend because this hot chick was really freaky and wanted a threesome with a couple. We hit on her for an hour or so, I left and he kept dancing with her, assuring her that his girlfriend wouldn’t mind. He brought her home and I just happened to never show up for the threesome.

21. ItsAllGolden

Distract-o-fucked his friend so my best friend could sneak off into the spare bedroom with him. Worst lay ever. He couldn’t get hard enough for the condom and when he finally did, he kind of just humped at me limply until he came. Did I mention we were on the floor of the study? His cat’s litter box was a foot from my face.

22. Seatb3lt

I started talking to a group of attractive girls at a party shortly before introducing my girlfriend. After a short while I began asking them about college sports…

Me: Do any of you watch college basketball?
Them: No. Not really.
Me: So you’ve never seen Princeton play? Them: No..?
Me: So you don’t recognize that dude over there? (Points to my tall friend Justin?)
Them: No. Should we?
Me: (To friend) Justin. Come here. Justin: Yes?
Me: I was just talking to these girls about how you got a full ride to Princeton as their starting point guard.

(This was before smart phones) His other friends kept coming up to him “congratulating him” on his scholarship while he has a girl on each knee, one rubbing his shoulders, and two more surrounding him all night.

23. Ferusomnium

With buddy at a bar, meet a guy and girl we thought were a couple, be social and find out not. The girl is clearly interested in my buddy, so I team up with other dude to go hunt. Find out he’s gay, and really likes my style. I owed my buddy big time for past events and he played the card. So I pretended to be bi-curious with the other dude, until the end of the night when my friend left with the girl. Then I calmly explained the situation, to which he responded “You give me a kiss right now, and I wont call her and cockblock your friend”

Bro-powers activate!

Gave the dude a powerkiss, he loved it, I realized how awful beards are to be face smashed against. Confirmed my heterosexuality and went home alone.

24. Rangers_fan812

In my senior year of college, I decided to visit my good friend (Brandon) who lives down in south carolina. One night while we were down there, my buddy suggested that we go to the five points and hit up some bars. The first two bars we go to, Brandon and I proceed to drink as many happy hour specials until we are both feeling pretty drunk. At that point, we decided to enter the third bar.

This bar was a little different than the others we were at before because the people were a lot older than us. Luckily, Brandon notices some of his friends standing by the bar and we join them. After about a half hour of standing around the bar, I notice that Brandon is gone. I look around, but the bar was pretty packed and I couldn’t find him.

I take my phone out to text him and I see that he’s sent me 5 text messages in the past 5 minutes. Most of them are pretty incoherent, but I can make out the words “bathroom” “hot cougars” “bruce karate.” After 5 more minutes of not seeing him anywhere around me, I decide to go check the bathrooms. As i’m walking up, I find Brandon doing his typical drunk stance trying to hit on these two 30+ year old women (we were both 22 then). He notices me walking up, and suddenly gets super excited and directs both girl’s attention to me.

I walk up, and he leans in for the weird drunk friend hug and whispers for me to play along. I soon find out that my friend told these girls that I was Bruce Lee’s son, and he was my trainer. He told them that I had just been casted into a new mega blockbuster karate movie and I was training a facility in South Carolina for the stunts. I stood there just grinning like a fool because I could not believe that these girls were eating his bullshit story up. So for the next hour and a half, I spoke with a slight asian accent, and did some karate kicks with the sound effects to prove to the girls that I was Bruce Lee’s son (and by karate kicks I mean i lifted up my leg while shrieking and waved my arms a little).

Anyways, we both ended up getting laid and to this day, I still consider that one of my greatest accomplishments.

25. metalman49

My buddy and I were drinking at this rural cemetery and he brought this girl that he hadn’t quite been able to get with yet. So he gets her drinking and she gets horny and the problem is I’m there and they have no privacy.

In my porn riddled brain I think wow maybe I can get in on this but my buddy comes up to me and asks me if I could go up to the front of the cemetery and stay there until they are finished.

So I sat in a dark rural cemetery by myself for 20 minutes drinking Jagermeister and contemplating jerking off to the sounds of my buddy and this girl fucking. I didn’t jerk off I just cried on the inside and drank my booze. Best lay he ever had and I third wheeled it in the dark.

26. scotteth

Walked 4.5 miles in a foot of January snow at 3 in the morning. Would still do it again.

27. nhexum

I had a friend that called into work, broke into my house, then washed my sheets and pillowcases and cleaned up a bit when he heard that a girl I was really, really into for a long time had finally agreed to come over shortly after work. I couldn’t take off work to get home early and wouldn’t have had enough time to do so otherwise.

Still my best friend to this day, even though it didn’t work out with the girl.

28. [deleted]

My best friend was going for a 2nd deployment in Iraq, so for a last night out, we go for some wings at a local sports bar we used to frequent.

He’s in army fatigues, I’m not in the army and not a damn person is paying him mind that he’s going back over there the next day. So, a liquored up me stands up and announces to the bar:

“This is my buddy, Otto Ottoson and tomorrow he’s going back to Iraq to help defend our freedom!”

Naturally, the bar became a crowd and gave thundering applause (It’s Texas, so major patriotism around these parts). People start buying him drinks, his bar tab is picked up along the way and no less than three women give him their phone number while I’m sitting back with a shit-eating grin on my face.

He ends up talking up two girls and taking a taxi home with the both of them- he told me the details and they were about as good as one could hope for. Back at the bar, I’m getting progressively more wasted and the bartender smirks at me and goes; “Don’t let no one tell you you ain’t serving your country, neither.” I guess getting a soldier a threesome is good enough service?

A few years later I was the best man at his wedding, so I guess we’re even.

29. technicolordreams

Piggyback-carried a girl to a friend house about half a mile away. Just kind of dropped her off as soon as we got in, crashed on the couch and said you two kids have fun. TC mark

image – Shutterstock

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